Macrocyclic tetra-NHC ligands are highly effective auxiliary ligands for a variety of oxidative transformations on first-row metals, such as aziridination.  To tune the effectiveness of the catalysis, several different sizes of macrocycle have been prepared including 16- and 18-atom variants, each of which has specific advantages for their respective iron complexes in terms of their reactivity.  The 16-atom versions are highly effective at stabilizing high oxidation state imides and tetrazenes but is not effective for catalytic aziridination.  However, these iron complexes react with both O-atom and PR-group transfer reagents.  Meanwhile, the 18-atom versions, which have been demonstrated to be highly active for catalytic aziridination, allow for the decoration with additional substituents on the ethyl bridge to generate chiral versions of the macrocycles.  These chiral macrocycles allow for the formation of novel high oxidation state iron alkylidenes directly from diazoalkanes.  Strategies for synthesis of all of these complexes and their future applications in oxidative group transfer reactions will be discussed.

What difference does an extra CH<sub>2</sub> make?  Oxidation chemistry of 16- and 18-atom ringed tetra-NHC iron complexes

2019 Fall National Meeting

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What difference does an extra CH2 make? Oxidation chemistry of 16- and 18-atom ringed tetra-NHC iron complexes

What difference does an extra CH₂ make? Oxidation chemistry of 16- and 18-atom ringed tetra-NHC iron complexes